Biphenyl carboxamides

ABSTRACT

Novel biphenylcarboxamides of the formula (I)  
                 
in which 
     R 1 , R 2 , m, n, R 3 , Y and A are as defined in the description, a plurality of processes for preparing these substances and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

The present invention relates to novel biphenylcarboxamides, to aplurality of processes for their preparation and to their use forcontrolling unwanted microorganisms.

It is already known that numerous carboxanilides have fungicidalproperties (compare WO 93/11 117, WO 99/09 013, WO 00/14 071, EP-A 0 545099 and EP-A 0 589 301). The activity of these substances is good;however, in some cases, for example at low application rates, it isunsatisfactory.

This invention now provides novel biphenylcarboxamides of the formula(I)

in which

-   R¹ and R² independently of one another represent hydrogen, halogen,    cyano, nitro, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio,    C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio having in    each case 1 to 13 fluorine, chlorine and/or bromine atoms,-   m represents 1, 2, 3 or 4, where R¹ represents identical or    different radicals if m represents 2, 3 or 4,-   n represents 1, 2 or 3, where R² represents identical or different    radicals if n represents 2 or 3,-   R³ represents hydrogen, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl,    C₁-C₆-haloalkyl having 1 to 7 halogen atoms, C₁-C₆-alkylamino,    C₁-C₆-alkylsulphenyl, C₁-C₆-haloalkylsulphenyl having 1 to 7 halogen    atoms, (C₁-C₆-alkyl)carbonyl, carbamoyl,-   Y represents carbonyl or represents C₁-C₃-alkylene which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy    and/or C₁-C₆-haloalkylthio having in each case 1 to 13 fluorine,    chlorine and/or bromine atoms and-   A represents a radical of the formula    where    -   R⁴ represents hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy having 1 to 5 halogen atoms,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio having 1 to 5 halogen        atoms, aminocarbonyl or aminocarbonyl-C₁-C₄-alkyl and    -   R⁵ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-alkoxy or C₁-C₄-alkylthio and    -   R⁶ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to        5 halogen atoms, hydroxy-C₁-C₄-alkyl, C₂-C₆-alkenyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl having 1 to 5 halogen atoms,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl having 1        to 5 halogen atoms or phenyl, or-   A represents a radical of the formula    where    -   R⁷ and R⁸ independently of one another represent hydrogen,        halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen        atoms and    -   R⁹ represents halogen, cyano or C₁-C₄-alkyl or C₁-C₄-haloalkoxy        having 1 to 5 halogen atoms, or-   A represents a radical of the formula    -   R¹⁰ and R¹¹ independently of one another represent hydrogen,        halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen        atoms and    -   R¹² represents hydrogen, C₁-C₄-alkyl or halogen, or-   A represents a radical of the formula    -   R¹³ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₆-alkyl,        C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-haloalkoxy        having 1 to 5 halogen atoms or C₁-C₄-haloalkylthio having 1 to 5        halogen atoms, or-   A represents a radical of the formula    -   R¹⁴ represents halogen, hydroxyl, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio having 1 to 5 halogen        atoms, or C₁-C₄-haloalkoxy having 1 to 5 halogen atoms and    -   R¹⁵ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkoxy having 1 to 5 halogen atoms,        C₁-C₄-alkylsulphinyl or C₁-C₄-alkylsulphonyl, or-   A represents a radical of the formula    -   R¹⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms and    -   R¹⁷ represents C₁-C₄-alkyl,    -   X¹ represents a sulphur atom, represents SO, SO₂ or CH₂,    -   p represents 0, 1 or 2, where R¹⁷ represents identical or        different radicals if p represents 2, or-   A represents a radical of the formula    -   R¹⁸ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms, or-   A represents a radical of the formula    -   R¹⁹ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms, or-   A represents a radical of the formula    -   R²⁰ represents halogen, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms,    -   R²¹ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms and    -   R²² represents hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl        having 1 to 5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl,        hydroxy-C₁-C₄-alkyl, C₁-C₄-alkylsulphonyl,        di(C₁-C₄-alkyl)aminosulphonyl, C₁-C₆-alkylcarbonyl or optionally        substituted phenylsulphonyl or benzoyl, or-   A represents a radical of the formula    -   R²³ and R²⁴ independently of one another represent hydrogen,        halogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms and    -   R²⁵ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms, or-   A represents a radical of the formula-   R²⁶ and R²⁷ independently of one another represent hydrogen,    halogen, amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5    halogen atoms and-   R²⁸ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms, or-   A represents a radical of the formula    -   R²⁹ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,        di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms and    -   R³⁰ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms, or-   A represents a radical of the formula    -   R³¹ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,        di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms and    -   R³² represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms, or-   A represents a radical of the formula    -   R³³ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms, or-   A represents a radical of the formula    -   R³⁴ represents hydrogen or C₁-C₄-alkyl and    -   R³⁵ represents halogen or C₁-C₄-alkyl, or-   A represents a radical of the formula    -   R³⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms, or-   A represents a radical of the formula    -   R³⁷ represents hydrogen, halogen or C₁-C₄-alkyl.

Depending on the nature of the substituents, the compounds of theformula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying compositions. The invention relates both tothe use of the pure isomers and to that of the isomer mixture.

Furthermore, it has been found that biphenylcarboxamides of the formula(I) are obtained when

-   a) carboxylic acid derivatives of the formula (II)    in which    -   A is as defined above and    -   G represents halogen, hydroxyl or C₁-C₆-alkoxy,    -   are reacted with aniline derivatives of the formula (III)        in which    -   R¹, R², m, n, R³ and Y are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of an acid binder and if appropriate in the        presence of a diluent, or-   b) carboxamide derivatives of the formula (IV)    in which    -   R¹, m, R³ and A are as defined above,    -   are reacted with boronic acid derivatives of the formula (V)        in which    -   R², n and Y are as defined above and    -   G¹ and G² each represent hydrogen or together represent        tetramethylethylene,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or-   c) carboxamide boronic acid derivatives of the formula (VI)    in which    -   R¹, m, R³ and A are as defined above and    -   G¹ and G² each represent hydrogen or together represent        tetramethylethylene,    -   are reacted with phenyl derivatives of the formula (VII)        in which    -   R², n and Y are as defined above,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or-   d) carboxamide derivatives of the formula (IV)    in which    -   R¹, m, R³ and A are as defined above,    -   are reacted with phenyl derivatives of the formula (VII)        in which    -   R², n and Y are as defined above,    -   in the presence of a palladium or platinum catalyst and in the        presence of        4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, if        appropriate in the presence of an acid binder and if appropriate        in the presence of a diluent.

Finally, it has been found that the novel biphenylcarboxamides of theformula (I) have very good microbicidal properties and can be used forcontrolling unwanted microorganisms both in crop protection and in theprotection of materials.

Surprisingly, the biphenylcarboxamides of the formula (I) according tothe invention have considerably better fungicidal activity than theconstitutionally most similar active compounds of the prior art havingthe same direction of action.

The formula (I) provides a general definition of thebiphenylcarboxamides according to the invention.

Preference is given to biphenylcarboxamides of the formula (I) in which

-   R¹ and R² independently of one another represent hydrogen, fluorine,    chlorine, bromine, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,    C₁-C₄-haloalkylthio having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms,-   m represents 1, 2 or 3, where R¹ represents identical or different    radicals if m represents 2 or 3,-   n represents 1, 2 or 3, where R² represents identical or different    radicals if n represents 2 or 3,-   R³ represents hydrogen, hydroxyl, C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₂-alkyl, cyano-C₁-C₄-alkyl,    C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-aminoalkyl,    C₁-C₄-alkylsulphenyl, C₁-C₄-haloalkylsulphenyl having 1 to 5 halogen    atoms, (C₁-C₄-alkyl)carbonyl,-   Y represents carbonyl or represents C₁-C₂-alkylene which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy and/or C₁-C₄-haloalkylthio having    in each case 1 to 9 fluorine, chlorine and/or bromine atoms, and-   A represents a radical of the formula    -   R⁴ represents hydrogen, cyano, fluorine, chlorine, bromine,        iodine, methyl, ethyl, i-propyl, C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy,        ethoxy, C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine and/or        bromine atoms, methylthio, ethylthio, trifluoromethylthio,        difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or        aminocarbonylethyl,    -   R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,        methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and    -   R⁶ represents hydrogen, methyl, ethyl, n-propyl, i-propyl,        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl,        cyclohexyl or phenyl, or-   A represents a radical of the formula    -   R⁷ and R⁸ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkyl        having 1 to 5 fluorine, chlorine and/or bromine atoms and    -   R⁹ represents fluorine, chlorine, bromine, cyano, methyl, ethyl        or C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine and/or        bromine atoms, or-   A represents a radical of the formula    -   R¹⁰ and R¹¹ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkyl        having 1 to 5 fluorine, chlorine and/or bromine atoms and    -   R¹² represents hydrogen, fluorine, chlorine, bromine, methyl or        ethyl, or-   A represents a radical of the formula    -   R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine,        hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms, C₁-C₂-haloalkoxy having        1 to 5 fluorine, chlorine and/or bromine atoms or        C₁-C₂-haloalkylthio having 1 to 5 fluorine, chlorine and/or        bromine atoms, or-   A represents a radical of the formula    -   R¹⁴ represents fluorine, chlorine, bromine, iodine, hydroxyl,        cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl having 1 to 5 fluorine,        chlorine and/or bromine atoms, methoxy, ethoxy, methylthio,        ethylthio, difluoromethylthio, trifluoromethylthio or        C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine        atoms and    -   R¹⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,        cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl having 1 to 5 fluorine,        chlorine and/or bromine atoms, methoxy, ethoxy, methylthio,        ethylthio, C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine        and/or bromine atoms, C₁-C₂-alkylsulphinyl or        C₁-C₂-alkylsulphonyl, or-   A represents a radical of the formula    -   R¹⁶ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms and    -   R¹⁷ represents methyl or ethyl,    -   X¹ represents a sulphur atom, represents SO, SO₂ or CH₂ and    -   p represents 0, 1 or 2, where R¹⁷ represents identical or        different radicals if p represents 2, or-   A represents a radical of the formula    -   R¹⁸ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms, or-   A represents a radical of the formula    -   R¹⁹ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms, or-   A represents a radical of the formula    -   R²⁰ represents fluorine, chlorine, bromine, cyano, methyl,        ethyl, i-propyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,        chlorine and/or bromine atoms,    -   R²¹ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or        bromine atoms and    -   R²² represents hydrogen, methyl, ethyl, C₁-C₂-haloalkyl having 1        to 5 fluorine, chlorine and/or bromine atoms,        C₁-C₂-alkoxy-C₁-C₂-alkyl, hydroxymethyl, hydroxyethyl,        methylsulphonyl or dimethylaminosulphonyl, or-   A represents a radical of the formula    -   R²³ and R²⁴ independently of one another represent hydrogen,        fluorine, chlorine, bromine, amino, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms and    -   R²⁵ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or        bromine atoms, or-   A represents a radical of the formula    -   R²⁶ and R²⁷ independently of one another represent hydrogen,        fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms and    -   R²⁸ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or        bromine atoms, or-   A represents a radical of the formula    -   R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,        C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms and    -   R³⁰ represents fluorine, chlorine, bromine, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms, or-   A represents a radical of the formula    -   R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,        C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms and    -   R³² represents fluorine, chlorine, bromine, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms, or-   A represents a radical of the formula    -   R³³ represents fluorine, chlorine, bromine, methyl, ethyl or        C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine        atoms, or-   A represents a radical of the formula    -   R³⁴ represents hydrogen, methyl or ethyl and    -   R³⁵ represents fluorine, chlorine, bromine, methyl or ethyl, or-   A represents a radical of the formula    -   R³⁶ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5        fluorine, chlorine and/or bromine atoms, or-   A represents a radical of the formula    -   R³⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or        ethyl.

Particular preference is given to biphenylcarboxamides of the formula(I) in which

-   R¹ and R² independently of one another represent hydrogen, fluorine,    chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl,    n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, difluoromethoxy, trifluoromethoxy,    trifluoromethylthio, difluorochloromethylthio,-   m represents 1 or 2, where R¹ represents identical or different    radicals if m represents 2,-   n represents 1 or 2, where R² represents identical or different    radicals if n represents 2,-   R³ represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl,    n-, i-, s-, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl,    difluoromethyl, methylsulphenyl, trichloromethylsulphenyl or acetyl,-   Y represents carbonyl or represents —CH₂— or —(CH₂)₂—, each of which    is optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, methyl, ethyl, i-propyl, t-butyl, methoxy, i-propoxy,    t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl,    trifluoromethoxy and trifluoromethylthio, and-   A represents a radical of the formula    -   R⁴ represents hydrogen, fluorine, chlorine, bromine, iodine,        methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl,        trifluoromethyl, difluorochloromethyl, trichloromethyl,        cyclopropyl, methoxy, ethoxy, trifluoromethoxy,        trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or        difluoromethylthio and    -   R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,        methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and    -   R⁶ represents hydrogen, methyl, ethyl, trifluoromethyl,        difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl, or-   A represents a radical of the formula    -   R⁷ and R⁸ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, difluorochloromethyl or trichloromethyl and    -   R⁹ represents fluorine, chlorine, bromine, cyano, methyl,        trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or        trichloromethoxy, or-   A represents a radical of the formula    -   R¹⁰ and R¹¹ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, difluorochloromethyl or trichloromethyl and    -   R¹² represents hydrogen, fluorine, chlorine, bromine, methyl or        ethyl, or-   A represents a radical of the formula    -   R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine,        hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl,        i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl,        difluorochloromethyl, trichloromethyl, trifluoromethoxy,        difluoromethoxy, difluorochloromethoxy, trichloromethoxy,        trifluoromethylthio, difluoromethylthio,        difluorochloromethylthio or trichloromethylthio, or-   A represents a radical of the formula    -   R¹⁴ represents fluorine, chlorine, bromine, iodine, hydroxyl,        cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,        s-butyl, t-butyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl, trichloromethyl, methoxy, ethoxy,        methylthio, ethylthio, difluoromethylthio, trifluoromethylthio,        trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or        trichloromethoxy and    -   R¹⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,        cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl,        trichloromethyl, methoxy, ethoxy, methylthio, ethylthio,        trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,        trichloromethoxy, methylsulphinyl or methylsulphonyl, or-   A represents a radical of the formula    -   R¹⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl or trichloromethyl and    -   R¹⁷ represents methyl or ethyl,    -   X¹ represents a sulphur atom, represents SO, SO₂ or CH₂ and    -   p represents 0, 1 or 2, where R¹⁷ represents identical or        different radicals if p represents 2, or-   A represents a radical of the formula    -   R¹⁸ represents methyl, ethyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R¹⁹ represents methyl, ethyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R²⁰ represents fluorine, chlorine, bromine, cyano, methyl,        ethyl, i-propyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl or trichloromethyl,    -   R²¹ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and    -   R²² represents hydrogen, methyl, ethyl, trifluoromethyl,        methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl, or-   A represents a radical of the formula    -   R²³ and R²⁴ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,        difluoromethyl, difluorochloromethyl or trichloromethyl and    -   R²⁵ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R²⁶ and R²⁷ independently of one another represent hydrogen,        fluorine, chlorine, bromine, nitro, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl and    -   R²⁸ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,        methylamino, dimethylamino, cyano, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl and    -   R³⁰ represents fluorine, chlorine, bromine, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,        methylamino, dimethylamino, cyano, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl and    -   R³² represents fluorine, chlorine, bromine, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R³³ represents fluorine, chlorine, bromine, methyl, ethyl,        trifluoromethyl, difluoromethyl, difluorochloromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R³⁴ represents hydrogen, methyl or ethyl and    -   R³⁵ represents fluorine, chlorine, bromine, methyl or ethyl, or-   A represents a radical of the formula    -   R³⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl,        difluorochloromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R³⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or        ethyl.

Very particular preference is given to biphenylcarboxamides of theformula (I) in which

-   R¹ and R² independently of one another represent hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl,    i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,    trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy,    trifluoromethylthio,-   m represents 1 or 2, where R¹ represents identical or different    radicals if m represents 2,-   n represents 1,-   R³ represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-,    s-, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl,-   Y represents carbonyl or represents —CH₂— or —(CH₂)₂—, each of which    is optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, methyl,    i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio,    i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy and    trifluoromethylthio, and-   A represents a radical of the formula    -   R⁴ represents hydrogen, fluorine, chlorine, bromine, iodine,        methyl, i-propyl, monofluoromethyl, difluoromethyl,        trifluoromethyl, difluorochloromethyl or trichloromethyl and    -   R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine or        methyl and    -   R⁶ represents hydrogen, methyl, trifluoromethyl or phenyl, or-   A represents a radical of the formula    -   R⁷ and R⁸ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl or trichloromethyl and    -   R⁹ represents fluorine, chlorine, bromine, methyl or        trifluoromethoxy, or-   A represents a radical of the formula    -   R¹⁰ and R¹¹ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl or trichloromethyl and    -   R¹² represents hydrogen, fluorine, chlorine, bromine or methyl,        or-   A represents a radical of the formula    -   R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine,        methyl, difluoromethyl, trifluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R¹⁴ represents fluorine, chlorine, bromine, iodine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl and    -   R¹⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,        n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,        trifluoromethyl, difluoromethyl, trichloromethyl,        methylsulphinyl or methylsulphonyl, or-   A represents a radical of the formula    -   R¹⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl or        trichloromethyl and    -   R¹⁷ represents methyl or ethyl,    -   X¹ represents a sulphur atom, represents SO, SO₂ or CH₂ and    -   p represents 0, 1 or 2, where R¹⁷ represents identical or        different radicals if p represents 2, or-   A represents a radical of the formula    -   R¹⁸ represents methyl, trifluoromethyl, difluoromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R¹⁹ represents methyl, trifluoromethyl, difluoromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R²⁰ represents fluorine, chlorine, bromine, methyl, i-propyl,        trifluoromethyl, difluoromethyl or trichloromethyl,    -   R²¹ represents hydrogen, fluorine, chlorine, bromine, methyl,        ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and    -   R²² represents hydrogen, methyl, ethyl, trifluoromethyl or        methoxymethyl, or-   A represents a radical of the formula    -   R²³ and R²⁴ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, trifluoromethyl,        difluoromethyl or trichloromethyl and    -   R²⁵ represents hydrogen, fluorine, chlorine, bromine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R²⁶ and R²⁷ independently of one another represent hydrogen,        fluorine, chlorine, bromine, methyl, trifluoromethyl,        difluoromethyl or trichloromethyl and    -   R²⁸ represents hydrogen, fluorine, chlorine, bromine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,        methylamino, dimethylamino, methyl, trifluoromethyl,        difluoromethyl or trichloromethyl and    -   R³⁰ represents fluorine, chlorine, bromine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,        methylamino, dimethylamino, methyl, trifluoromethyl,        difluoromethyl or trichloromethyl and    -   R³² represents fluorine, chlorine, bromine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R³³ represents fluorine, chlorine, bromine, methyl,        trifluoromethyl, difluoromethyl or trichloromethyl, or-   A represents a radical of the formula    -   R³⁴ represents hydrogen, methyl or ethyl and    -   R³⁵ represents fluorine, chlorine, bromine, methyl or ethyl, or-   A represents a radical of the formula    -   R³⁶ represents methyl, trifluoromethyl, difluoromethyl or        trichloromethyl, or-   A represents a radical of the formula    -   R³⁷ represents hydrogen, fluorine, chlorine, bromine or methyl.

Especially preferred are biphenylcarboxamides of the formula (I) inwhich

-   R¹ represents hydrogen, fluorine, chlorine, methyl,-   R² represents hydrogen,-   m represents 1 or 2, where R¹ represents identical or different    radicals if m represents 2,-   n represents 1,-   R³ represents hydrogen,-   Y represents —CH₂—, —(CH₂)₂—, —CF₂— or —(CF₂)₂—, and-   A represents a radical of the formula    -   R⁴ represents methyl, monofluoromethyl, difluoromethyl or        trifluoromethyl and    -   R⁵ represents hydrogen, fluorine, chlorine or methyl and    -   R⁶ represents methyl, or-   A represents a radical of the formula    -   R⁷ and R⁸ represent hydrogen and    -   R⁹ represents methyl, or-   A represents a radical of the formula    -   R¹⁰ and R¹¹ represent hydrogen and    -   R¹² represents methyl, or-   A represents a radical of the formula    -   R¹³ represents iodine, methyl, difluoromethyl or        trifluoromethyl, or-   A represents a radical of the formula    -   R²⁰ represents methyl, trifluoromethyl or difluoromethyl,    -   R²¹ represents hydrogen, fluorine, chlorine, methyl,        trifluoromethyl or difluoromethyl and    -   R²² represents hydrogen, methyl, ethyl, trifluoromethyl or        methoxymethyl, or-   A represents a radical of the formula    -   R²³ and R²⁴ represent hydrogen and    -   R²⁵ represents methyl, or-   A represents a radical of the formula    -   R²⁶ and R²⁷ represent hydrogen and    -   R²⁸ represents methyl, or-   A represents a radical of the formula    -   R²⁹ represents amino, methylamino, dimethylamino, methyl or        trifluoromethyl and    -   R³⁰ represents methyl, trifluoromethyl or difluoromethyl, or-   A represents a radical of the formula    -   R³¹ represents amino, methylamino, dimethylamino, methyl or        trifluoromethyl and    -   R³² represents methyl, trifluoromethyl or difluoromethyl, or-   A represents a radical of the formula    -   R³⁶ represents methyl or trifluoromethyl.

Moreover, emphasis is given to compounds of the formula (I) in which R³represents hydrogen.

Moreover, emphasis is given to compounds of the formula (I) in which R²represents hydrogen.

Moreover, emphasis is given to compounds of the formula (I) in which Yrepresents —CH₂—, —(CH₂)₂—, —CF₂— or —(CF₂)₂—.

Moreover, emphasis is given to compounds of the formula (I) in which R¹represents hydrogen, fluorine, chlorine or methyl and especiallyhydrogen or fluorine.

Moreover, emphasis is given to compounds of the formula (I) in which mrepresents 0, 1 or 2.

Moreover, emphasis is given to compounds of the formula (I) in which Arepresents a radical of the formula

where R⁴, R⁵ and R⁶ are as defined above.

Moreover, emphasis is given to compounds of the formula (I) in which Arepresents a radical of the formula

where R⁷, R⁸ and R⁹ are as defined above.

Moreover, emphasis is given to compounds of the formula (I) in which Arepresents a radical of the formula

where R¹³ is as defined above.

Moreover, emphasis is given to compounds of the formula (I) in which Arepresents a radical of the formula

where R²⁹ and R³⁰ are as defined above.

Moreover, emphasis is given to compounds of the formula (I) in which Arepresents a radical of the formula

where R³⁶ is as defined above.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, even in combination with heteroatoms, such as, for example, inalkoxy.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitutions the substituents can be identical ordifferent.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono-or polyhalogenated. In the case of polyhalogenation, the halogen atomscan be identical or different. Here, halogen represents fluorine,chlorine, bromine and iodine, in particular fluorine, chlorine andbromine.

However, the general or preferred radical definitions or illustrationslisted above can also be combined with one another as desired, i.e.including combinations between the respective ranges and preferredranges. They apply to the end products and, correspondingly, toprecursors and intermediates. Moreover, individual definitions may notapply.

Using 2-methyl-4-trifluoromethyl-1,3-thiazole-5-carbonyl chloride and(2,2-difluoro-1,3-benzodioxol-5-yl)phenylamine as starting materials,the course of the process (a) according to the invention can beillustrated by the formula scheme below.

Using N-(2-bromophenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideand 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-ylboronic acid asstarting materials and a catalyst, the course of the process (b)according to the invention can be illustrated by the formula schemebelow.

Using2-{[(5-fluoro-1,3-dimethyl-1H-pyrazol-4-yl)carbonyl]amino}phenylboronicacid and 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxine asstarting materials and a catalyst, the course of the process (c)according to the invention can be illustrated by the formula schemebelow.

Using N-(2-bromophenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideand 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxine as startingmaterials and a catalyst and4,4,4′,4′,5,5,5,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, the courseof the process (d) according to the invention can be illustrated by theformula scheme below.

Explanation of the Processes and Intermediates

The formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the process(a) according to the invention. In this formula, A preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals. G preferablyrepresents chlorine, bromine, hydroxyl, methoxy or ethoxy, particularlypreferably chlorine, hydroxy or methoxy.

The carboxylic acid derivatives of the formula (II) are known or can beprepared by known processes (cf. WO 93/11 117, EP-A 0 545 099, EP-A 0589 301 and EP-A 0 589 313).

The formula (III) provides a general definition of the anilinederivatives required as reaction components for carrying out the process(a) according to the invention. In this formula, R¹, R², m, n, R³ and Ypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred or especially preferred for these radicalsor these indices.

The aniline derivatives of the formula (III) are novel. Some of them canbe prepared by known methods (cf. EP-A 0 545 099 and EP-A 0 589 301).Moreover, aniline derivatives of the formula (III) are obtained by

-   e) reacting 2-haloaniline derivatives of the general formula (VIII)    in which    -   R¹, m and R³ are as defined above and    -   Hal represents halogen,    -   with boronic acid derivatives of the formula (V)        in which    -   R², n, Y, G¹ and G² are as defined above,    -   if appropriate in the presence of an acid binder, and if        appropriate in the presence of an inert organic diluent, and if        appropriate in the presence of a catalyst, or-   f) reacting anilineboronic acids of the formula (IX)    in which    -   R¹, m, R³, G¹ and G² are as defined above,    -   with phenyl derivatives of the formula (VII)        in which    -   R², n and Y are as defined above,    -   if appropriate in the presence of an acid binder, and if        appropriate in the presence of an inert organic diluent, and if        appropriate in the presence of a catalyst.

The formula (VIII) provides a general definition of the 2-haloanilinederivatives required as reaction components for carrying out the process(e) according to the invention. In this formula, R¹, m and R³ preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals or these indices.Hal preferably represents fluorine, chlorine or bromine, particularlypreferably chlorine or bromine.

The 2-haloaniline derivatives of the formula (VIII) are known and/or canbe prepared from the corresponding nitro compounds by reduction. If R³does not represent hydrogen, the compounds of the formula (VIII) can beobtained by known derivatizations of the resulting aniline derivatives.

The boronic acid derivatives of the formula (V) furthermore required asstarting materials for carrying out the process (e) according to theinvention are illustrated in more detail below, in connection with theprocess (b) according to the invention.

The formula (IX) provides a general definition of the anilineboronicacids required as reaction components for carrying out the process (f)according to the invention. In this formula, R¹, m and R³ preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred, very particularlypreferred or especially preferred for these radicals or these indices.G¹ and G² preferably each represent hydrogen or together representtetramethylethylene.

The anilineboronic acids of the formula (IX) are known and/or can beobtained by known methods.

The phenyl derivatives of the formula (VIII) furthermore required asstarting materials for carrying out the process (f) according to theinvention are illustrated in more detail below, in connection with theprocess (d) according to the invention.

The formula (IV) provides a general definition of the carboxamidederivatives required as starting materials for carrying out the process(b) and (d) according to the invention. In this formula, R¹, m, R³ and Apreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred or especially preferred for these radicalsor these indices.

The carboxamide derivatives of the formula (IV) are known or can beprepared by known processes (cf., for example, WO 91/01311, EP-A 0 371950).

The formula (V) provides a general definition of the boronic acidderivatives required as starting materials for carrying out theprocesses (b) and (e) according to the invention. In this formula, R², nand Y preferably have those meanings which have already been mentionedin connection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,very particularly preferred or especially preferred for these radicalsor these indices. G¹ and G² preferably each represent hydrogen ortogether represent tetramethylethylene.

The boronic acid derivatives of the formula (V) are known and/or can beprepared by known processes (cf., for example, WO 01/90084 and U.S. Pat.No. 5,633,218). They are obtained, for example, by

-   g) reacting phenyl derivatives of the formula (VII)    in which    -   R², n and Y are as defined above,    -   with boric acid esters of the formula (X)        B(OR³⁸)₃  (X)        in which    -   R³⁸ represents C₁-C₄-alkyl,    -   in the presence of magnesium, if appropriate in the presence of        a diluent (for example tetrahydrofuran).

The formula (X) provides a general definition of the boric acid estersrequired as reaction components for carrying out the process (g)according to the invention. In this formula, R³⁸ preferably representsmethyl, ethyl, n- or i-propyl, particularly preferably methyl or ethyl.

The boric acid esters of the formula (X) are known chemicals forsynthesis.

The formula (VI) provides a general definition of the carboxamideboronic acid derivatives required as reaction components for carryingout the process (c) according to the invention. In this formula, R¹, m,R³ and A preferably have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred, very particularly preferred or especially preferred for theseradicals or these indices. G¹ and G² preferably each represent hydrogenor together represent tetramethylethylene.

The carboxamide boronic acid derivatives of the formula (VI) are knownand/or can be prepared by known processes.

The formula (VII) provides a general definition of the phenylderivatives required as starting materials for carrying out theprocesses (c), (d), (f) and (g) according to the invention. In thisformula, R², n and Y preferably have those meanings which have alreadybeen mentioned in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred,particularly preferred, very particularly preferred or especiallypreferred for these radicals or these indices.

The phenyl derivatives of the formula (VII) are known or can be preparedby known processes (cf. Synth. Commun. 2000, 30, 665-669, Synth. Commun.1999, 29, 1697-1701).

Suitable acid binders for carrying out the processes (a), (b), (c), (d),(e) and (f) according to the invention are in each case all inorganicand organic bases customary for such reactions. Preference is given tousing alkaline earth metal or alkali metal hydroxides, such as sodiumhydroxide, calcium hydroxide, potassium hydroxide, or else ammoniumhydroxide, alkali metal carbonates, such as sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate, alkali metal oralkaline earth metal acetates, such as sodium acetate, potassiumacetate, calcium acetate, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,pyridine, N-methylpiperidine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU). However, it is also possible to work in theabsence of an additional acid binder, or to employ an excess of theamine component so that it simultaneously acts as acid binder.

Suitable diluents for carrying out the processes (a), (b), (c), (d), (e)and (f) according to the invention are in each case all customary inertorganic solvents. Preference is given to using optionally halogenatedaliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether,hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene,xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate, sulphoxides, such asdimethylsulphoxide, or sulphones, such as sulpholane.

When carrying out the processes (a), (b), (c), (d), (e) and (f)according to the invention, the reaction temperatures can in each casebe varied within a relatively wide range. In general, the processes arecarried out at temperatures between 0° C. and 140° C., preferablybetween 10° C. and 120° C.

The processes (a), (b), (c), (d), (e) and (f) according to the inventionare generally each carried out under atmospheric pressure. However, ineach case it is also possible to operate under elevated or reducedpressure.

When carrying out the process (a) according to the invention, in general1 mol or else an excess of aniline derivative of the formula (III) andfrom 1 to 3 mol of acid binder are employed per mole of acid halide ofthe formula (II). However, it is also possible to employ the reactioncomponents in other ratios. Work-up is carried out by customary methods.In general, water is added to the reaction mixture and the organic phaseis separated off and, after drying, concentrated under reduced pressure.The residue that remains may, if appropriate, be freed of any impuritiesthat may still be present using customary methods, such aschromatography or recrystallization.

When carrying out the process (b) according to the invention, in general1 mol or else an excess of boronic acid derivative of the formula (V)and from 1 to 5 mol of acid binder are employed per mole of carboxamideof the formula (IV). However, it is also possible to employ the reactioncomponents in other ratios. Work-up is carried out by customary methods.In general, water is added to the reaction mixture and the precipitateis separated off and dried. The residue that remains may, ifappropriate, be freed of any impurities that may still be present usingcustomary methods, such as chromatography or recrystallization.

When carrying out the process (c) according to the invention, in general1 mol or else an excess of phenyl derivative of the formula (VII) andfrom 1 to 10 mol of acid binder and from 0.5 to 5 mol % of a catalystare employed per mole of carboxamide boronic acid derivative of theformula (VI). However, it is also possible to employ the reactioncomponents in other ratios. Work-up is carried out by customary methods.In general, water is added to the reaction mixture and the precipitateis separated off and dried. The residue that remains may, ifappropriate, be freed of any impurities that may still be present usingcustomary methods, such as chromatography or recrystallization.

When carrying out the process (d) according to the invention, in general1 mol or else an excess of phenyl derivative of the formula (VII) andfrom 1 to 5 mol of acid binder and from 1 to 5 mol of a catalyst areemployed per mole of carboxamide derivative of the formula (IV).However, it is also possible to employ the reaction components in otherratios. Work-up is carried out by customary methods. In general, wateris added to the reaction mixture and the precipitate is separated offand dried. The residue that remains may, if appropriate, be freed of anyimpurities that may still be present using customary methods, such aschromatography or recrystallization.

The substances according to the invention have potent microbicidalactivity and can be employed for controlling unwanted microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

-   Xanthomonas species, such as, for example, Xanthomonas campestris    pv. oryzae;-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Pythium species, such as, for example, Pythium ultimum;-   Phytophthora species, such as, for example, Phytophthora infestans;-   Pseudoperonospora species, such as, for example, Pseudoperonospora    humuli or Pseudoperonospora cubensis;-   Plasmopara species, such as, for example, Plasmopara viticola;-   Bremia species, such as, for example, Bremia lactucae;-   Peronospora species, such as, for example, Peronospora pisi or P.    brassicae;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Botrytis species, such as, for example, Botrytis cinerea;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Altemaria species, such as, for example, Alternaria brassicae; and-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

The active compounds according to the invention also show a stronginvigorating action in plants. Accordingly, they are suitable formobilizing the internal defences of the plant against attack by unwantedmicroorganisms.

In the present context, plant-invigorating (resistance-inducing)compounds are to be understood as meaning substances which are capableof stimulating the defence system of plants such that, when the treatedplants are subsequently inoculated with unwanted microorganisms, theydisplay substantial resistance to these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. The compoundsaccording to the invention can thus be used to protect plants within acertain period of time after treatment against attack by the pathogensmentioned. The period of time for which this protection is achievedgenerally extends for 1 to 10 days, preferably 1 to 7 days, from thetreatment of the plants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

If appropriate, the active compounds according to the invention can, atcertain concentrations and application rates, also be employed asherbicides, for regulating plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates orprecursors in the synthesis of other active compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations, such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested material and vegetative and generative propagation material,for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormultilayer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, unwanted microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be tackifiers, sizes, paper and board, textiles,leather, wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably tackifiers, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis,-   Aspergillus, such as Aspergillus niger,-   Chaetomium, such as Chaetomium globosum,-   Coniophora, such as Coniophora puetana,-   Lentinus, such as Lentinus tigrinus,-   Penicillium, such as Penicillium glaucum,-   Polyporus, such as Polyporus versicolor,-   Aureobasidium, such as Aureobasidium pullulans,-   Sclerophoma, such as Sclerophoma pityophila,-   Trichoderma, such as Trichoderma viride,-   Escherichia, such as Escherichia coli,-   Pseudomonas, such as Pseudomonas aeruginosa, and-   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can, as such or in theirformulations, also be used in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Suitable mixing components are, for example, the following compounds:

Fungicides:

-   2-phenylphenol; 8-hydroxyquinoline sulphate;-   acibenzolar-5-methyl; aldimorph; amidoflumet; ampropylfos;    ampropylfos-potassium; andoprim; anilazine; azaconazole;    azoxystrobin;-   benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl;    benzamacril; benzamacrilisobutyl; bilanafos; binapacryl; biphenyl;    bitertanol; blasticidin-S; bromuconazole; bupirimate; buthiobate;    butylamine;-   calcium polysulphide; capsimycin; captafol; captan; carbendazim;    carboxin; carpropamid; carvone; chinomethionat; chlobenthiazone;    chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon;    cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil;    cyprofuram;-   Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;    diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole;    diflumetorim; dimethirimol; dimethomorph; dimoxystrobin;    diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione;    ditalimfos; dithianon; dodine; drazoxolon;-   edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;-   famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole;    fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil;    fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine;    fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin;    fluquinconazole; flurprimidol; flusilazole; flusulphamide;    flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium;    fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox;-   guazatine; hexachlorobenzene; hexaconazole; hymexazole;-   imazalil; imibenconazole; iminoctadine triacetate; iminoctadine    tris(albesil); iodocarb; ipconazole; iprobenfos; iprodione;    iprovalicarb; irumamycin; isoprothiolane; isovaledione;-   kasugamycin; kresoxim-methyl;-   mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl;    metalaxyl-M; metconazole; methasulphocarb; methfuroxam; metiram;    metominostrobin; metsulphovax; mildiomycin; myclobutanil;    myclozolin;-   natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol;-   ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;    oxycarboxin; oxyfenthiin;-   paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen;    phthalide; picoxystrobin; piperalin; polyoxins; polyoxorim;    probenazole; prochloraz; procymidone; propamocarb;    propanosine-sodium; propiconazole; propineb; proquinazid;    prothioconazole; pyraclostrobin; pyrazophos; pyrifenox;    pyrimethanil; pyroquilon; pyroxyfur; pyrrolenitrine;-   quinconazole; quinoxyfen; quintozene; simeconazole; spiroxamine;    sulphur; tebuconazole; tecloftalam; tecnazene; tetcyclacis;    tetraconazole; thiabendazole; thicyofen; thifluzamide;    thiophanate-methyl; thiram; tioxymid; tolclofos-methyl;    tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide;    tricyclamide; tricyclazole; tridemorph; trifloxystrobin;    triflumizole; triforine; triticonazole;-   uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide;-   (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;-   1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;-   2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;-   2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;-   3,4,5-trichloro-2,6-pyridinedicarbonitrile;-   actinovate;    cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;-   monopotassium carbonate;-   N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;-   N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine;-   sodium tetrathiocarbonate;    and copper salts and preparations, such as Bordeaux mixture; copper    hydroxide; copper naphthenate; copper oxychloride; copper sulphate;    cufraneb; copper oxide; mancopper; oxine-copper.    Bactericides:    bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/Acaricides/Nematicides:-   abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,    acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,    aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin    (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin,    AZ-60541, azadirachtin, azamethiphos, azinphos-methyl,    azinphos-ethyl, azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus    thuringiensis strain GC-91, Bacillus thuringiensis strain    NCTC-11821, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin,    beta-cypermethrin, bifenazate, bifenthrin, binapacryl, bioallethrin,    bioallethrin-5-cyclopentylisomer, bioethanomethrin, biopermethrin,    bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl,    bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505,    bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim,    butylpyridaben,-   cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,    carbosulphan, cartap, CGA-50439, chinomethionat, chlordane,    chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,    chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,    chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos    (-ethyl), chlovaporthrin, chromafenozide, cis-cypermethrin,    cis-resmethrin, cis-permethrin, clocythrin, cloethocarb,    clofentezine, clothianidin, clothiazoben, codlemone, coumaphos,    cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella,    cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin    (1R-trans-isomer), cyromazine,-   DDT, deltamethrin, demeton-5-methyl, demeton-5-methylsulphone,    diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos,    dicofol, dicrotophos, dicyclanil, diflubenzuron, dimethoate,    dimethylvinphos, dinobuton, dinocap, dinotefuran, diofenolan,    disulphoton, docusat-sodium, dofenapyn, DOWCO-439,-   eflusilanate, emamectin, emamectin-benzoate, empenthrin (1R-isomer),    endosulphan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb,    ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,-   famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin,    fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb,    fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate,    fensulphothion, fenthion, fentrifanil, fenvalerate, fipronil,    flonicamid, fluacrypyrim, fluazuron, flubenzimine, flubrocythrinate,    flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox,    flumethrin, flupyrazofos, flutenzin (flufenzine), fluvalinate,    fonofos, formetanate, formothion, fosmethilan, fosthiazate,    fubfenprox (fluproxyfen), furathiocarb,-   gamma-HCH, gossyplure, grandlure, granulosis viruses,-   halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,    hexythiazox, hydramethylnone, hydroprene,-   IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos,    iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion,    ivermectin,-   japonilure, kadethrin, nuclear polyhedrosis viruses, kinoprene,-   lambda-cyhalothrin, lindane, lufenuron,-   malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium,    methacrifos, methamidophos, Metharhizium anisopliae, Metharhizium    flavoviride, methidathion, methiocarb, methomyl, methoprene,    methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,    milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos,    moxidectin, MTI-800,-   naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide,    nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250,    NNI-9768, novaluron, noviflumuron,-   OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate,    oxamyl, oxydemeton-methyl,-   Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl),    permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans    isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,    phosphocarb, phoxim, piperonyl butoxide, pirimicarb,    pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos,    promecarb, propaphos, propargite, propetamphos, propoxur,    prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos,    pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion,    pyridathion, pyrimidifen, pyriproxyfen,-   quinalphos, resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,-   S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad,    spirodiclofen, spiromesifen, sulphlurarnid, sulphotep, sulprofos,    SZI-121,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbam, terbufos,    tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin    (1R-isomer), tetrasul, theta-cypermethrin, thiacloprid,    thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate,    thiodicarb, thiofanox, thiometon, thiosultap-sodium, thuringiensin,    tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene,    triazamate, triazophos, triazuron, trichlophenidine, trichlorfon,    triflumuron, trimethacarb,-   vamidothion, vaniliprole, verbutin, Verticillium lecanii,-   WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, xylylcarb,-   ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,-   the compound 3-methylphenyl propylcarbamate (tsumacide Z),-   the compound    3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-octane-3-carbonitrile    (CAS-Reg. No. 185982-80-3) and the corresponding 3-endoisomer    (CAS-Reg. No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),    and preparations which comprise insecticidally active plant    extracts, nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, safeners and/or semiochemicals isalso possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes,Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi does by no means limit the mycotic spectrum which can becovered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5,000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof, are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized are in particular increased defence ofthe plants against insects by toxins formed in the plants, in particularthose formed in the plants by the genetic material from Bacillusthuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c),CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and alsocombinations thereof) (hereinbelow referred to as “Bt plants”). Traitsthat are also particularly emphasized are the increased defence of theplants against fungi, bacteria and viruses by systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and resistance genesand correspondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned also include thevarieties sold under the name Clearfield® (for example maize). Ofcourse, these statements also apply to plant cultivars which have thesegenetic traits or genetic traits still to be developed, and which willbe developed and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

9.77 g of cesium carbonate and 2 ml of water are added to a solution of3.12 g ofN-(2-bromophenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide and3.28 g of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-ylboronicacid (V-1) in 10 ml of n-butanol. With stirring and under an atmosphereof argon, 60 mg of tetrakis-(triphenylphosphine)palladium(0) are added.The reaction mixture is stirred at 80° C. for 8 h. For work-up, themixture is poured into water and extracted with ethyl acetate and theextract is dried and concentrated. The residue is chromatographed onsilica gel (cyclohexane/ethyl acetate 2:1).

This gives 4.00 g (83% of theory) of5-fluoro-1,3-dimethyl-N-[2-(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-1H-pyrazole-4-carboxamidein the form of a colourless solid [logP (pH 2.3)=3.77].

Example 2

Under argon, 0.37 g (1.6 mmol) of 5-bromo-2,2-difluoro-1,3-benzodioxole,0.4 g (1.6 mmol) of4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane and 0.42 g(4.3 mmol) of potassium acetate are suspended in 5 ml of dimethylsulphoxide, and 0.05 g (0.07 mmol) of1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride is added.After 2 h at 80° C., the mixture is cooled to room temperature, and 0.51g (1.3 mmol) ofN-(2-iodophenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-carboxamide(IV-1), 3.25 ml of a 2 M solution of sodium carbonate and a further 0.05g (0.07 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)chloride are added. After 45 min at 70° C., the mixture is diluted with5 ml of water and extracted 3 times with in each case 50 ml of ethylacetate. The extracts are dried over sodium sulphate, filtered andconcentrated under reduced pressure. The crude product is taken up indiethyl ether and chromatographed on silica gel (cyclohexane/ethylacetate 3:1).

This gives 0.23 g (41% of theory) ofN-[2-(2,2-difluoro-1,3-benzodioxol-5-yl)-phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-carboxamide[logP (pH 2.3)=3.37].

The biphenylcarboxamides of the formula (I) listed in Table 1 below arelikewise prepared analogously to Examples 1 and 2 described above and inaccordance with the general descriptions of the processes. TABLE 1 (I)

logP Ex. R¹ _(m) R² _(n) R³ Y A (pH2.3) 3 H H H —CF₂—

3.94 4 H H H —CF₂—

3.99 5 H H H —CF₂—

3.81 6 H H H —(CF₂)₂—

5.93 7 H H H —(CF₂)₂—

4.08 8 H H H —(CF₂)₂—

3.85 9 H H H —(CF₂)₂—

4.46 10 H H H —(CF₂)₂—

3.94 11 4,5-F₂ H H —CH₂—

3.24 12 4-Cl H H —CH₂—

3.32 13 4-CH₃, 5-F H H —CH₂—

3.37 14 5-CH₃ H H —CH₂—

3.01 15 4,6-F₂ H H —CH₂—

2.34 16 4-CH₃ H H —CH₂—

3.10 17 4-F, 6-Cl H H —CH₂—

2.53 18 4-Cl, 6-F H H —CH₂—

2.74 19 H H H —CF₂—

3.22 20 H H H —CH₂—

2.87 21 H H Me —(CF₂)₂—

3.44Preparation of Starting Materials of the Formula (IV)

Example (IV-1)

6.57 g (30.0 mmol) of 2-iodoaniline and 6.1 g (60.0 mmol) oftriethylamine are dissolved in 100 ml of tetrahydrofuran and, at roomtemperature, 7.65 g (36.0 mmol) of1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride are addedslowly. The reaction solution is heated at 50° C. for 16 h. For work-up,the mixture is concentrated under reduced pressure and the crude productis chromatographed on silica gel (cyclohexane/ethyl acetate 1:1).

This gives 10.0 g (85% of theory) ofN-(2-iodophenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide[logP (pH 2.3)=2.46].

Preparation of Starting Materials of the Formula (V)

Example (V-1)

A few grains of iodine are added to a suspension of 4.86 g of magnesiumturnings in 20 ml of tetrahydrofuran (anhydrous), and 57.4 g of6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxine in 60 ml oftetrahydrofuran are then added dropwise under an atmosphere of argon. Byadjusting the rate of the dropwise addition, the exothermic reaction ismaintained close to the boiling point. After the dropwise addition hasended, the mixture is stirred under reflux for 30 min and then cooled toroom temperature. The solution of the Grignard reagent is, together witha solution of 29.2 g of triethyl borate in 60 ml of tetrahydrofuran,added dropwise, at −10° C. and over a period of 30 min, to 100 ml oftetrahydrofuran. The mixture is then stirred at −10° C. for another 1 hand then warmed to room temperature and stirred for another 30 min. Forwork-up, the reaction solution is, at −10° C., hydrolysed with 14 ml ofwater and adjusted to pH 4 using 80 ml of 10% strength sulphuric acid.The mixture is extracted with diethyl ether and the aqueous phase issaturated with sodium chloride and extracted with diethyl ether. Thecombined ether phases are, together with 200 ml of water, concentrated.The solid residue is triturated with a little methylene chloride,filtered off with suction and dried.

This gives 47.3 g (75% of theory) of2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl-boronic acid [logP(pH 2.3)=2.49].

The logP values given in the Preparation Examples were determined inaccordance with EEC Directive 79/831 Annex V.A8 by HPLC (HighPerformance Liquid Chromatography) using a reversed-phase column (C 18).Temperature: 43° C.

Mobile phases for the determination in the acidic range: 0.1% aqueousphosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

USE EXAMPLES Example A

Podosphaera Test (Apple)/Protective

Solvents:

-   -   24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide        Emulsifier:    -   1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the apple mildew pathogen Podosphaera leucotricha.The plants are then placed in a greenhouse at about 23° C. and arelative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE A Podosphaera test (apple)/protective Appli- cationrate of active compound Efficacy Active compound in g/ha in % 2

100 100 3

100 100 5

100 100 6

100 100 9

100 100 10

100 100 19

100 100 1

100 100

Example B

Sphaerotheca Test (Cucumber)/Protective

Solvents:

-   -   24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide        Emulsifier:    -   1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE B Sphaerotheca test (cucumber)/protective Appli-cation rate of active compound Efficacy Active compound in g/ha in % 2

100 100 3

100 98 4

100 100 5

100 100 6

100 100 9

100 100 10

100 100 19

100 92 1

100 98

Example C

Venturia Test (Apple)/Protective

Solvents:

-   -   24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide        Emulsifier:    -   1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. in 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE C Venturia test (apple)/protective Appli- cation rateof active compound Efficacy Active compound in g/ha in % 2

100 100 4

100 98 5

100 100 6

100 99 10

100 100 19

100 96 1

100 100

Example D

Alternaria Test (Tomato)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Alternaria solani and then remain at 100% relative humidity and at20° C. for 24 h. The plants then remain at 96% relative atmospherichumidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE D Alternaria test (tomato)/protective Applicationrate of active compound in Efficacy Active compound g/ha in % 2

750 100 3

750 94 9

750 95 15

750 95

Example E

Puccinia Test (Wheat)/Protective

-   Solvent: 25 parts by weight of N,N-dimethylacetamide-   Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE E Puccinia test (wheat)/protective Appli- cation rateof active compound Efficacy Active compound in g/ha in % 1

500 100

Example F

Inhibitory Test Using a Giant Colony of Basidiomycetes

Mycelium pieces were punched out of a giant colony of the Basidiomycetesspecies Coriolus versicolor and incubated at 26° C. on a nutrient agarmedium containing malt extract peptone. The inhibition of the growth ofthe fungal threads on active-compound-containing nutrient media wascompared to the longitudinal growth on nutrient media without addedactive compound and rated as inhibition in percent.

In this test, for example, the following compounds according to theinvention of the Preparation Examples show good activity: TABLE FInhibitory test using a giant colony of Basidiomycetes Application rateof active Inhi- compound in bition Active compound ppm ppm 19

6 100 1

6 100

1. Biphenylcarboxamides of the formula (I)

in which R¹ and R² independently of one another represent hydrogen,halogen, cyano, nitro, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio,C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio having in eachcase 1 to 13 fluorine, chlorine and/or bromine atoms, m represents 1, 2,3 or 4, where R¹ represents identical or different radicals if mrepresents 2, 3 or 4, n represents 1, 2 or 3, where R² representsidentical or different radicals if n represents 2 or 3, R³ representshydrogen, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₈-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-haloalkyl having 1 to7 halogen atoms, C₁-C₆-alkylamino, C₁-C₆-alkylsulphenyl,C₁-C₆-haloalkylsulphenyl having 1 to 7 halogen atoms,(C₁-C₆-alkyl)carbonyl, carbamoyl, Y represents carbonyl or representsC₁-C₃-alkylene which is optionally mono- or polysubstituted by identicalor different substituents from the group consisting of halogen,C₁-C₆-alkyl, C₃-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy and/or C₁-C₆-haloalkylthio having in each case 1 to 13fluorine, chlorine and/or bromine atoms and A represents a radical ofthe formula

R⁴ represents hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl,C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy having 1 to 5 halogen atoms,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio having 1 to 5 halogen atoms,aminocarbonyl or aminocarbonyl-C₁-C₄-alkyl and R⁵ represents hydrogen,halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio and R⁶represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 halogenatoms, hydroxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkylthio-C₁-C₄-alkyl having 1 to5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkylhaving 1 to 5 halogen atoms or phenyl, or A represents a radical of theformula

R⁷ and R⁸ independently of one another represent hydrogen, halogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms and R⁹represents halogen, cyano or C₁-C₄-alkyl or C₁-C₄-haloalkoxy having 1 to5 halogen atoms, or A represents a radical of the formula

R¹⁰ and R¹¹ independently of one another represent hydrogen, halogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms and R¹²represents hydrogen, C₁-C₄-alkyl or halogen, or A represents a radicalof the formula

R¹³ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₆-alkyl,C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-haloalkoxy having 1to 5 halogen atoms or C₁-C₄-haloalkylthio having 1 to 5 halogen atoms,or A represents a radical of the formula

R¹⁴ represents halogen, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkylhaving 1 to 5 halogen atoms, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio having 1 to 5 halogen atoms, or C₁-C₄-haloalkoxyhaving 1 to 5 halogen atoms and R¹⁵ represents hydrogen, halogen, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkoxy having 1 to 5 halogen atoms,C₁-C₄-alkylsulphinyl or C₁-C₄-alkylsulphonyl, or A represents a radicalof the formula

R¹⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogenatoms and R¹⁷ represents C₁-C₄-alkyl, X¹ represents a sulphur atom,represents SO, SO₂ or CH₂, p represents 0, 1 or 2, where R¹⁷ representsidentical or different radicals if p represents 2, or A represents aradical of the formula

R¹⁸ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogenatoms, or A represents a radical of the formula

R¹⁹ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogenatoms, or A represents a radical of the formula

R²⁰ represents halogen, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1to 5 halogen atoms, R²¹ represents hydrogen, halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl having 1 to 5 halogen atoms and R²² represents hydrogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 halogen atoms,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkylsulphonyl,di(C₁-C₄-alkyl)-aminosulphonyl, C₁-C₆-alkylcarbonyl or optionallysubstituted phenylsulphonyl or benzoyl, or A represents a radical of theformula

R²³ and R²⁴ independently of one another represent hydrogen, halogen,amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms andR²⁵ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having1 to 5 halogen atoms, or A represents a radical of the formula

R²⁶ and R²⁷ independently of one another represent hydrogen, halogen,amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atomsand R²⁸ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkylhaving 1 to 5 halogen atoms, or A represents a radical of the formula

R²⁹ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to5 halogen atoms and R³⁰ represents halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radicalof the formula

R³¹ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to5 halogen atoms and R³² represents halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radicalof the formula

R³³ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5halogen atoms, or A represents a radical of the formula

R³⁴ represents hydrogen or C₁-C₄-alkyl and R³⁵ represents halogen orC₁-C₄-alkyl, or A represents a radical of the formula

R³⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogenatoms, or A represents a radical of the formula

R³⁷ represents hydrogen, halogen or C₁-C₄-alkyl.
 2. Biphenylcarboxamidesof the formula (I) according to claim 1 in which R¹ and R² independentlyof one another represent hydrogen, fluorine, chlorine, bromine, cyano,nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio having in each case 1 to 9fluorine, chlorine and/or bromine atoms, m represents 1, 2 or 3, whereR¹ represents identical or different radicals if m represents 2 or 3, nrepresents 1, 2 or 3, where R² represents identical or differentradicals if n represents 2 or 3, R³ represents hydrogen, hydroxyl,C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₂-alkyl,cyano-C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 halogen atoms,C₁-C₄-aminoalkyl, C₁-C₄-alkylsulphenyl, C₁-C₄-haloalkylsulphenyl having1 to 5 halogen atoms, (C₁-C₄-alkyl)carbonyl, Y represents carbonyl orrepresents C₁-C₂-alkylene which is optionally mono- or polysubstitutedby identical or different substituents from the group consisting offluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy and/or C₁-C₄-haloalkylthio having ineach case 1 to 9 fluorine, chlorine and/or bromine atoms, and Arepresents a radical of the formula

R⁴ represents hydrogen, cyano, fluorine, chlorine, bromine, iodine,methyl, ethyl, i-propyl, C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy,C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms,methylthio, ethylthio, trifluoromethylthio, difluoromethylthio,aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl, R⁵ representshydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy,ethoxy, methylthio or ethylthio and R⁶ represents hydrogen, methyl,ethyl, n-propyl, i-propyl, C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,cyclopentyl, cyclohexyl or phenyl, or A represents a radical of theformula

R⁷ and R⁸ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5fluorine, chlorine and/or bromine atoms and R⁹ represents fluorine,chlorine, bromine, cyano, methyl, ethyl or C₁-C₂-haloalkoxy having 1 to5 fluorine, chlorine and/or bromine atoms, or A represents a radical ofthe formula

R¹⁰ and R¹¹ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5fluorine, chlorine and/or bromine atoms and R¹² represents hydrogen,fluorine, chlorine, bromine, methyl or ethyl, or A represents a radicalof the formula

R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl,cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorineand/or bromine atoms, C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorineand/or bromine atoms or C₁-C₂-haloalkylthio having 1 to 5 fluorine,chlorine and/or bromine atoms, or A represents a radical of the formula

R¹⁴ represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano,C₁-C₄-alkyl, C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/orbromine atoms, methoxy, ethoxy, methylthio, ethylthio,difluoromethylthio, trifluoromethylthio or C₁-C₂-haloalkoxy having 1 to5 fluorine, chlorine and/or bromine atoms and R¹⁵ represents hydrogen,fluorine, chlorine, bromine, iodine, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkylhaving 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy,methylthio, ethylthio, C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorineand/or bromine atoms, C₁-C₂-alkylsulphinyl or C₁-C₂-alkylsulphonyl, or Arepresents a radical of the formula

R¹⁶ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms and R¹⁷ represents methyl or ethyl, X¹represents a sulphur atom, represents SO, SO₂ or CH₂ and p represents 0,1 or 2, where R¹⁷ represents identical or different radicals if prepresents 2, or A represents a radical of the formula

R¹⁸ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, or A represents a radical of the formula

R¹⁹ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, or A represents a radical of the formula

R²⁰ represents fluorine, chlorine, bromine, cyano, methyl, ethyl,i-propyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/orbromine atoms, R²¹ represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/orbromine atoms and R²² represents hydrogen, methyl, ethyl,C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,C₁-C₂-alkoxy-C₁-C₂-alkyl, hydroxymethyl, hydroxyethyl, methylsulphonylor dimethylaminosulphonyl, or A represents a radical of the formula

R²³ and R²⁴ independently of one another represent hydrogen, fluorine,chlorine, bromine, amino, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5fluorine, chlorine and/or bromine atoms and R²⁵ represents hydrogen,fluorine, chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkyl having 1to 5 fluorine, chlorine and/or bromine atoms, or A represents a radicalof the formula

R²⁶ and R²⁷ independently of one another represent hydrogen, fluorine,chlorine, bromine, amino, nitro, methyl, ethyl or C₁-C₂-haloalkyl having1 to 5 fluorine, chlorine and/or bromine atoms and R²⁸ representshydrogen, fluorine, chlorine, bromine, methyl, ethyl or C₁-C₂-haloalkylhaving 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents aradical of the formula

R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl orC₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atomsand R³⁰ represents fluorine, chlorine, bromine, methyl, ethyl orC₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,or A represents a radical of the formula

R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl orC₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atomsand R³² represents fluorine, chlorine, bromine, methyl, ethyl orC₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,or A represents a radical of the formula

R³³ represents fluorine, chlorine, bromine, methyl, ethyl orC₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,or A represents a radical of the formula

R³⁴ represents hydrogen, methyl or ethyl and R³⁵ represents fluorine,chlorine, bromine, methyl or ethyl, or A represents a radical of theformula

R³⁶ represents methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, or A represents a radical of the formula

R³⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.3. Biphenylcarboxamides of the formula (I) according to claim 1 in whichR¹ and R² independently of one another represent hydrogen, fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl,n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio,ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, difluorochloromethylthio, m represents 1 or 2,where R¹ represents identical or different radicals if m represents 2, nrepresents 1 or 2, where R² represents identical or different radicalsif n represents 2, R³ represents hydrogen, hydroxyl, methyl, ethyl,n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl,difluoromethyl, methylsulphenyl, trichloromethylsulphenyl or acetyl, Yrepresents carbonyl or represents —CH₂— or —(CH₂)₂—, each of which isoptionally mono- to tetrasubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy,methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxyand trifluoromethylthio, and A represents a radical of the formula

R⁴ represents hydrogen, fluorine, chlorine, bromine, iodine, methyl,ethyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl,difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy,trifluoromethoxy, trichloromethoxy, methylthio, ethylthio,trifluoromethylthio or difluoromethylthio and R⁵ represents hydrogen,fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,methylthio or ethylthio and R⁶ represents hydrogen, methyl, ethyl,trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl,or A represents a radical of the formula

R⁷ and R⁸ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,difluorochloromethyl or trichloromethyl and R⁹ represents fluorine,chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy or trichloromethoxy, or A represents a radical ofthe formula

R¹⁰ and R¹¹ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,difluorochloromethyl or trichloromethyl and R¹² represents hydrogen,fluorine, chlorine, bromine, methyl or ethyl, or A represents a radicalof the formula

R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl,cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl,t-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl,trichloromethyl, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy, trichloromethoxy, trifluoromethylthio,difluoromethylthio, difluorochloromethylthio or trichloromethylthio, orA represents a radical of the formula

R¹⁴ represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano,methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl,methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio,trifluoromethylthio, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy or trichloromethoxy and R¹⁵ represents hydrogen,fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl,i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio,ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,trichloromethoxy, methylsulphinyl or methylsulphonyl, or A represents aradical of the formula

R¹⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl and R¹⁷ represents methyl orethyl, X¹ represents a sulphur atom, represents SO, SO₂ or CH₂ and prepresents 0, 1 or 2, where R¹⁷ represents identical or differentradicals if p represents 2, or A represents a radical of the formula

R¹⁸ represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl, or A represents a radical ofthe formula

R¹⁹ represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl, or A represents a radical ofthe formula

R²⁰ represents fluorine, chlorine, bromine, cyano, methyl, ethyl,i-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl, R²¹ represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl andR²² represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl,ethoxymethyl, hydroxymethyl or hydroxyethyl, or A represents a radicalof the formula

R²³ and R²⁴ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl and R²⁵ represents hydrogen,fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl, or A representsa radical of the formula

R²⁶ and R²⁷ independently of one another represent hydrogen, fluorine,chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and R²⁸represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl, or A represents a radical of the formula

R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and R³⁰represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl, or A representsa radical of the formula

R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and R³²represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl, or A representsa radical of the formula

R³³ represents fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl, or A represents a radical of the formula

R³⁴ represents hydrogen, methyl or ethyl and R³⁵ represents fluorine,chlorine, bromine, methyl or ethyl, or A represents a radical of theformula

R³⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl, or A represents a radical ofthe formula

R³⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.4. Biphenylcarboxamides of the formula (I) according to claim 1 in whichR¹ and R² independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio,trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy,trifluoromethylthio, m represents 1 or 2, where R¹ represents identicalor different radicals if m represents 2, n represents 1, R³ representshydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl,cyclopropyl, cyclopentyl or cyclohexyl, Y represents carbonyl orrepresents —CH₂— or —(CH₂)₂—, each of which is optionally mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i-propoxy,t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl,trifluoromethoxy and trifluoromethylthio, and A represents a radical ofthe formula

R⁴ represents hydrogen, fluorine, chlorine, bromine, iodine, methyl,i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl,difluorochloromethyl or trichloromethyl and R⁵ represents hydrogen,fluorine, chlorine, bromine, iodine or methyl and R⁶ representshydrogen, methyl, trifluoromethyl or phenyl, or A represents a radicalof the formula

R⁷ and R⁸ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl ortrichloromethyl and R⁹ represents fluorine, chlorine, bromine, methyl ortrifluoromethoxy, or A represents a radical of the formula

R¹⁰ and R¹¹ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl ortrichloromethyl and R¹² represents hydrogen, fluorine, chlorine, bromineor methyl, or A represents a radical of the formula

R¹³ represents hydrogen, fluorine, chlorine, bromine, iodine, methyl,difluoromethyl, trifluoromethyl or trichloromethyl, or A represents aradical of the formula

R¹⁴ represents fluorine, chlorine, bromine, iodine, methyl,trifluoromethyl, difluoromethyl or trichloromethyl and R¹⁵ representshydrogen, fluorine, chlorine, bromine, iodine, n-propyl, i-propyl,n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl,trichloromethyl, methylsulphinyl or methylsulphonyl, or A represents aradical of the formula

R¹⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl ortrichloromethyl and R¹⁷ represents methyl or ethyl, X¹ represents asulphur atom, represents SO, SO₂ or CH₂ and p represents 0, 1 or 2,where R¹⁷ represents identical or different radicals if p represents 2,or A represents a radical of the formula

R¹⁸ represents methyl, trifluoromethyl, difluoromethyl ortrichloromethyl, or A represents a radical of the formula

R¹⁹ represents methyl, trifluoromethyl, difluoromethyl ortrichloromethyl, or A represents a radical of the formula

R²⁰ represents fluorine, chlorine, bromine, methyl, i-propyl,trifluoromethyl, difluoromethyl or trichloromethyl, R²¹ representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl or trichloromethyl and R²² represents hydrogen, methyl,ethyl, trifluoromethyl or methoxymethyl, or A represents a radical ofthe formula

R²³ and R²⁴ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, trifluoromethyl, difluoromethyl ortrichloromethyl and R²⁵ represents hydrogen, fluorine, chlorine,bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, orA represents a radical of the formula

R²⁶ and R²⁷ independently of one another represent hydrogen, fluorine,chlorine, bromine, methyl, trifluoromethyl, difluoromethyl ortrichloromethyl and R²⁸ represents hydrogen, fluorine, chlorine,bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, orA represents a radical of the formula

R²⁹ represents hydrogen, fluorine, chlorine, bromine, amino,methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl ortrichloromethyl and R³⁰ represents fluorine, chlorine, bromine, methyl,trifluoromethyl, difluoromethyl or trichloromethyl, or A represents aradical of the formula

R³¹ represents hydrogen, fluorine, chlorine, bromine, amino,methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl ortrichloromethyl and R³² represents fluorine, chlorine, bromine, methyl,trifluoromethyl, difluoromethyl or trichloromethyl, or A represents aradical of the formula

R³³ represents fluorine, chlorine, bromine, methyl, trifluoromethyl,difluoromethyl or trichloromethyl, or A represents a radical of theformula

R³⁴ represents hydrogen, methyl or ethyl and R³⁵ represents fluorine,chlorine, bromine, methyl or ethyl, or A represents a radical of theformula

R³⁶ represents methyl, trifluoromethyl, difluoromethyl ortrichloromethyl, or A represents a radical of the formula

R³⁷ represents hydrogen, fluorine, chlorine, bromine or methyl. 5.Biphenylcarboxamides of the formula (I) according to claim 1 in which R¹represents hydrogen, fluorine, chlorine, methyl, R² represents hydrogen,m represents 1 or 2, where R¹ represents identical or different radicalsif m represents 2, n represents 1, R³ represents hydrogen, Y represents—CH₂—, —(CH₂)₂—, —CF₂— or —(CF₂)₂—, and A represents a radical of theformula

R⁴ represents methyl, monofluoromethyl, difluoromethyl ortrifluoromethyl and R⁵ represents hydrogen, fluorine, chlorine or methyland R⁶ represents methyl, or A represents a radical of the formula

R⁷ and R⁸ represent hydrogen and R⁹ represents methyl, or A represents aradical of the formula

R¹⁰ and R¹¹ represent hydrogen and R¹² represents methyl, or Arepresents a radical of the formula

R¹³ represents iodine, methyl, difluoromethyl or trifluoromethyl, or Arepresents a radical of the formula

R²⁰ represents methyl, trifluoromethyl or difluoromethyl, R²¹ representshydrogen, fluorine, chlorine, methyl, trifluoromethyl or difluoromethyland R²² represents hydrogen, methyl, ethyl, trifluoromethyl ormethoxymethyl, or A represents a radical of the formula

R²³ and R²⁴ represent hydrogen and R²⁵ represents methyl, or Arepresents a radical of the formula

R²⁶ and R²⁷ represent hydrogen and R²⁸ represents methyl, or Arepresents a radical of the formula

R²⁹ represents amino, methylamino, dimethylamino, methyl ortrifluoromethyl and R³⁰ represents methyl, trifluoromethyl ordifluoromethyl, or A represents a radical of the formula

R³¹ represents amino, methylamino, dimethylamino, methyl ortrifluoromethyl and R³² represents methyl, trifluoromethyl ordifluoromethyl, or A represents a radical of the formula

R³⁶ represents methyl or trifluoromethyl.
 6. Process for preparingbiphenylcarboxamides of the formula (I) according to claim 1,characterized in that a) carboxylic acid derivatives of the formula (II)

in which A is as defined in claim 1 and G represents halogen, hydroxylor C₁-C₆-alkoxy, are reacted with aniline derivatives of the formula(III)

in which R¹, R², m, n, R³ and Y are as defined in claim 1, ifappropriate in the presence of a catalyst, if appropriate in thepresence of an acid binder and if appropriate in the presence of adiluent, or b) carboxamide derivatives of the formula (IV)

in which R¹, m, R³ and A are as defined in claim 1, are reacted withboronic acid derivatives of the formula (V)

in which R², n and Y are as defined in claim 1 and G¹ and G² eachrepresent hydrogen or together represent tetramethylethylene, in thepresence of a catalyst, if appropriate in the presence of an acid binderand if appropriate in the presence of a diluent, or c) carboxamideboronic acid derivatives of the formula (VI)

in which R¹, m, R³ and A are as defined in claim 1 and G¹ and G² eachrepresent hydrogen or together represent tetramethylethylene, arereacted with phenyl derivatives of the formula (VII)

in which R², n and Y are as defined in claim 1, in the presence of acatalyst, if appropriate in the presence of an acid binder and ifappropriate in the presence of a diluent, or d) carboxamide derivativesof the formula (IV)

in which R¹, m, R³ and A are as defined in claim 1, are reacted withphenyl derivatives of the formula (VII)

in which R², n and Y are as defined in claim 1, in the presence of apalladium or platinum catalyst and in the presence of4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, ifappropriate in the presence of an acid binder and if appropriate in thepresence of a diluent.
 7. Compositions for controlling unwantedmicroorganisms, characterized in that they comprise at least onebiphenylcarboxamide of the formula (I) according to claim 1, in additionto extenders and/or surfactants.
 8. Use of biphenylcarboxamides of theformula (I) according to claim 1 for controlling unwantedmicroorganisms.
 9. Method for controlling unwanted microorganisms,characterized in that biphenylcarboxamides of the formula (I) accordingto claim 1 are applied to the microorganisms and/or their habitats. 10.Process for preparing compositions for controlling unwantedmicroorganisms, characterized in that biphenylcarboxamides of theformula (I) according to claim 1 are mixed with extenders and/orsurfactants.
 11. Aniline derivatives of the formula (III)

in which R¹, R², m, n, R³ and Y are as defined in claim 1.